Planta Med 2017; 83(17): 1329-1334
DOI: 10.1055/s-0043-109567
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Denudatin A, a Dimeric Acylphloroglucinol from Hypericum denudatum Presents an Antinociceptive Effect in Mice

Henrique Bridi
1   Programa de Pós Graduação em Ciências Farmacêuticas, Universidade Federal do Rio Grande do Sul, Porto Alegre, Brazil
,
Gabriela de Carvalho Meirelles
1   Programa de Pós Graduação em Ciências Farmacêuticas, Universidade Federal do Rio Grande do Sul, Porto Alegre, Brazil
,
Sérgio Augusto de Loreto Bordignon
2   Programa de Pós Graduação em Avaliação de Impactos Ambientais, UNILASALLE, Canoas, Brazil
,
Stela Maris Kuze Rates
1   Programa de Pós Graduação em Ciências Farmacêuticas, Universidade Federal do Rio Grande do Sul, Porto Alegre, Brazil
,
Gilsane Lino von Poser
1   Programa de Pós Graduação em Ciências Farmacêuticas, Universidade Federal do Rio Grande do Sul, Porto Alegre, Brazil
› Institutsangaben
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Publikationsverlauf

received 27. Januar 2017
revised 05. April 2017

accepted 19. April 2017

Publikationsdatum:
04. Mai 2017 (online)

Abstract

A new dimeric acylphloroglucinol, denudatin A (1), was isolated from the flowering aerials parts of Hypericum denudatum, along with the known phloroglucinols selancin A (2), hyperbrasilol A (3), uliginosin B (4), and isouliginosin B (5). The structure of 1 was elucidated using 1D, 2D NMR, and MS experiments, and by comparison with previously reported data for Hypericum dimeric acylphloroglucinols. Denudatin A (1) and selancin A (2) were administered orally to mice displaying antinociceptive activity in the hot plate test. The compounds did not induce motor impairment in the rotarod apparatus.

Supporting Information

 
  • References

  • 1 Ccana-Ccapatinta GV, Barros FMC, Bridi H, von Poser GL. Dimeric acylphloroglucinols in Hypericum species from sections Brathys and Trigynobrathys . Phytochem Rev 2015; 14: 25-50
  • 2 Ccana-Ccapatinta GV, von Poser GL. Acylphloroglucinol derivatives from Hypericum laricifolium Juss. Phytochem Lett 2015; 12: 63-68
  • 3 Bridi H, Ccana-Ccapatinta GV, Stolz ED, Meirelles GC, Bordignon SAL, Rates SMK, von Poser GL. Dimeric acylphloroglucinols from Hypericum austrobrasiliense exhibiting antinociceptive activity in mice. Phytochemistry 2016; 122: 178-183
  • 4 Ferraz ABF, Bordignon SAL, Staats C, Schripsema J, von Poser GL. Benzopyrans from Hypericum polyanthemum . Phytochemistry 2001; 57: 1227-1230
  • 5 Bernardi APM, Ferraz ABF, Albring DV, Bordignon SAL, Schripsema J, Bridi R, Dutra-Filho CS, Henriques AT, von Poser GL. Benzophenones from Hypericum carinatum . J Nat Prod 2005; 68: 784-786
  • 6 Rocha L, Marston A, Kaplan MAC, Stoeckli-Evans H, Thull U, Testa B, Hostettmann K. An antifungal γ-pyrone and xanthones with monoamine oxidase inhibitory activity from Hypericum brasiliense . Phytochemistry 1994; 36: 1381-1385
  • 7 Rocha L, Marston A, Potterat O, Kaplan MAC, Stoeckli-Evans H, Hostettmann K. Antibacterial phloroglucinols and flavonoids from Hypericum brasiliense . Phytochemistry 1995; 40: 1447-1452
  • 8 Stein AC, Viana AF, Müller LG, Nunes JM, Stolz ED, do Rego JC, Costentin J, von Poser GL, Rates SMK. Uliginosin B, a phloroglucinol derivative from Hypericum polyanthemum: a promising new molecular pattern for the development of antidepressant drugs. Behav Brain Res 2012; 228: 66-73
  • 9 Ccana-Ccapatinta GV, Stolz ED, da Costa PF, Rates SMK, von Poser GL. Acylphloroglucinol derivatives from Hypericum andinum: antidepressant-like activity of andinin A. J Nat Prod 2014; 77: 2321-2325
  • 10 Haas JS, Viana AF, Heckler APM, von Poser GL, Rates SMK. The antinociceptive effect of a benzopyran (HP1) isolated from Hypericum polyanthemum in mice hot-plate test is blocked by naloxone. Planta Med 2010; 76: 1419-1423
  • 11 Stolz ED, Hasse DR, von Poser GL, Rates SMK. Uliginosin B, a natural phloroglucinol derivative, presents a multimediated antinociceptive effect in mice. J Pharm Pharmacol 2014; 66: 1774-1785
  • 12 Stolz ED, Müller LG, Antonio CB, Da Costa PF, von Poser GL, Noël F, Rates SMK. Determination of pharmacological interactions of uliginosin B, a natural phloroglucinol derivative, with amitriptiline, clonidine and morphine by isobolographic analysis. Phytomedicine 2014; 21: 1684-1688
  • 13 Stolz ED, Viana AF, Hasse DR, von Poser GL, do Rego JC, Rates SMK. Uliginosin B presents antinociceptive effect mediated by dopaminergic and opioid systems in mice. Prog Neuropsycopharmacol Biol Psychiatry 2012; 39: 80-87
  • 14 Robson NKB. Studies in the genus Hypericum L. (Guttiferae) 8. Sections 29. Brathys (part 2) and 30. Trigynobrathys . Bull Br Mus Nat Hist 1990; 20: 1-151
  • 15 Robson NKB. Studies in the genus Hypericum L. (Hypericaceae) 9. Addenda, corrigenda, keys, lists and general discussion. Phytotaxa 2012; 72: 1-111
  • 16 Fobofou SAT, Franke K, Porzel A, Brandt W, Wessjohann LA. Tricyclic acylphloroglucinols from Hypericum lanceolatum and regioselective synthesis of selancins A and B. J Nat Prod 2016; 79: 743-753
  • 17 Parker WL, Johnson FJ. The structure determination of antibiotic compounds from Hypericum uliginosum . J Am Chem Soc 1968; 90: 4716-4723
  • 18 Gu GM, Feng SZ, Wang XY. The isolation and structure of japonicine A, B, C, D. Acta Chim Sinica 1988; 46: 246-257
  • 19 Henry G, Raithore S, Zhang Y, Jayaprakasa B, Nair MG, Heber D, Seeram NP. Acylphloroglucinol derivatives from Hypericum prolificum . J Nat Prod 2006; 69: 1645-1648
  • 20 Winkelmann K, San M, Kypriotakis Z, Skaltsa H, Bosilij B, Heilmann J. Antibacterial and citotoxic activity of prenylated bicyclic acylphloglucinol derivatives from Hypericum amblycalyx . Z Naturforsch 2003; 58: 527-532
  • 21 Crispin MC, Hur M, Park T, Kim YH, Wurtele ES. Identification and biosynthesis of acylphloroglucinols in Hypericum gentianoides . Physiol Plant 2013; 148: 354-370
  • 22 Meirelles GC. Potenciação da ação de produtos lipofílicos provenientes de espécies de Hypericum nativas do sul do Brasil [Dissertation]. Porto Alegre: Universidade Federal do Rio Grande do Sul; 2016
  • 23 Brasil, Congresso Nacional. 2008 Lei procedimentos para o uso científico de animais. Lei n. 11794. Diário Oficial da União, 8 de outubro de 2008. .
  • 24 Brasil, Ministério da Ciência, Tecnologia e Inovação, CONCEA, 2013a. Diretriz brasileira para o cuidado e a utilização de animais para fins científicos e didáticos – DBCA. Portaria n. 465 de 23 de maio de 2013. .
  • 25 Brasil, Ministério da Ciência. Diretrizes da prática de eutanásia do CONCEA. Portaria n. 596 de 25 de junho de 2013. .